Trityl chloride → 1-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

HRID 901120Notes

Reaction equation

HRID 901120 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[N:3]=[CH:2]1.Cl[C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(CC)CC>CN(C=O)C>[C:13]1([C:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:1]2[CH:5]=[C:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[N:3]=[CH:2]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418812HCID 178418812, compound

Product 1

HCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl esterYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Step 4.a. (3.2 g, 17.5 mmol) in DMF (50 ml) was treated with chlorotriphenylmethane (4.88 g, 17.5 mmol) and Et3N (5.4 ml, 38.5 mmol) and the reaction was stirred at room temperature for about 6 hours. The DMF was evaporated under reduced pressure and the residue was distributed between EtOAc and saturated NaCl solution. The EtOAc layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield product as a viscous oil (6.96 g, 104%) which crystallized on standing. Mass spec. 383.3 MH+.

Workup

  1. customThe DMF was evaporated under reduced pressure
  2. dry with materialThe EtOAc layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37d9b375895a401297b8968b39a8222e
Source dataset
uspto-grants-2008_04
Patent number
US07361656B2

Reaction notes

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